Letting Go is Hard to Do
by NeoCortex
Summary: This story is multi-chaptered and my attempt at dipping my toe into the waters of the shipping of Destiel and Sabriel. Will be eventual Wincest. Rated M for later chapters. Slow going at first. Fair warning.
1. Chapter 1

Sam lay in his bed staring up at the dark ceiling. The room surrounding him was quiet. The only real noise was what could be heard through the wall that connected his room to his brother's. And that noise was not something he really wanted to hear.

A solitary tear ran down his cheek as Sam rolled to bury his face in his pillow now. He hated having to hear those sounds. Sounds of his brother that way for someone else. Sounds of the man he loved loving and being loved by another. Sounds of Dean being brought to pleasure again and again; night after night at the hands of Castiel.

Dean's cries of pleasure as he bellows out Cas' name cover the noise of Sam sobbing into his pillow for the umpteenth time in the last six months.


	2. Chapter 2

He entered the kitchen the next morning unable to look at his brother- not for the first time- as he fought to keep his eyes from watering.

"Hey Sammy, you look like hell. Did you get any sleep last night?"

Dean sounded a bit too cheery and that rubbed Sam wrong.

"No, not really..." He grunted as he yanked a beer from the fridge and started for the living room instead of staying in the same room as the man that was breaking his heart and didn't even know it.

"Beer, Sam? Isn't it a bit early for that?"

"You wanna be the pot, or the kettle?" He grumbled snappishly as he trudged away.


	3. Chapter 3

Dean entered Sam's room with a loud knock only to find a man that wasn't his brother sprawled across Sam's bed.

"Um, Gabriel? Why are you in Sam's bed?"

"Well I could give you the answer to that, but I'm sure you can connect the dots..." Was the snarky reply as the sheet slipped down the Arch Angel's very naked back as the man rolled to look at Dean.

Dean was about to answer when the bathroom door down the hall opened and a cloud of steam filed out engulfing Sam as he gripped at the corners of the towel at his waist.

Green eyes were met with cold hollow hazel as the younger brother sauntered towards him. "Ya need somethin' Dean?" The voice was rough and not the way Dean was used to it sounding.

"Uh, yeah, but it's not important, Sammy. It can wait."

"Alright. And it's Sam." The last was followed by the bedroom door closing in his face leaving a very confused and oddly heart aching Dean in the silent hallway.

What was he missing here?


	4. Chapter 4

"Dean, I am uncertain what you are so worried about." Castiel frowned up at his human lover as he paced back and forth across the room in agitation.

"He's screwing around with Gabriel! An Arch Angel for crying out loud!"

"Dean, I am an Angel. Aren't we screwing around too?" He was really confused at the moment.

"No, Cas, what we do is different. What we have is different."

"And how do you know that what he has with Gabriel isn't different as well?"

This seemed to agitate Dean even more for he scoffed and threw his arms up in the air, "I doubt that very seriously! After all that Gabriel has done to us! To HIM!" He was clearly talking about Sam's 100 Tuesdays when Dean sold his soul.

"Dean, I feel compelled to add that I too have put you and Sam through some horrible things. Yet you seem able to forgive me for them. Is Sam not allowed to do the same with my brother?" He was really confused by his lover's double standards. But then humans still confused him anyway.

"I never said he wasn't allowed to forgive him!" Dean didn't seem to realize he was digging himself into a bit of a hole.

"But he's just not allowed to have feelings for him?"

"No! I mean, yes! I mean- damn it! I don't know anymore!" Dean threw his arms into the air and dropped down to the couch in frustration letting out a heavy sigh. "I just don't get it Cas. What does Sammy see in the dick?"

"Did ya ever stop ta think that maybe what Sammy and I have is a mutually beneficial relationship?" Dean started and looked up to the living room door. Gabriel stood there, hands in his pockets looking for all the world as if he owned it all. What Gabriel said caused Dean to cock his head to the side- he really didn't like the way the dick said his brother's personal nickname.

"Neither of us can have what we really want," His eyes were on Cas as he spoke before he turned to look at Dean now, "So we settle for what we can have and we make it work."

Dean was confused now. "What do you mean you can't have what you really want?"

"It's more like we can't have /who/ we really want, but eh- semantics." Gabriel looked over at the clock, "Well I gotta be off. Other people's lives to mess with and all." He gave a jaunty wave that appeared to be rather put upon as he vanished from sight before Dean could finish his demanding question.

"Damn it Gabriel! Get back here! I'm not done talking to you."

"It would appear that you are Dean." Cas commented a little more dryly than normal.

"What the hell was that supposed to mean? Why can't they have who they really want?" He was so utterly confused that his head was starting to hurt.


	5. Chapter 5

Sam's eyes were so hollow as they looked back at Dean. This made the other feel guilty. And he had no idea why. He'd not done anything wrong had he? No. He'd been nice to his brother and given him anything he'd asked for hadn't he? So why was Sam looking at him as if he'd killed his puppy?

"Sam, what's wrong? I mean, every time you look at me I get this distinct feeling that you hate me."

"I don't hate you Dean." Sam replied with a tone so hollow it made his eyes seem alight with joy. "Quite the opposite really. Not that it really matters."

That last was said so quietly Dean wasn't even really sure that he'd actually heard it. "Well then what's wrong? If something's up you know I'll help you."

"You can't fix this Dean. Just leave it be." Sam's voice held such finality to it that Dean had no choice but to sigh and agree.

Getting up from the table they sat at he started to leave their kitchen but not before stopping at Sam's side and placing a hand gently on his shoulder and squeezing tightly, "You know I love you right Sammy?"

"Yeah, Dean, I know." There was something in his voice that sounded off but Dean didn't want to push anything too far. Squeezing Sam's shoulder one last time Dean nodded and left the younger Winchester alone in the kitchen not seeing the tears streaming down his baby brother's face as he left.

"Just not the way I love you."


	6. Chapter 6

The house was quiet; Dean had run into town to get groceries for him and Sam. Cas and Sam were apparently the only ones in the house.

Castiel had been walking past Sam's bedroom door when he heard it.

What sounded like Samuel sobbing. Frowning he cocked his head to the side and stood in silence and listened to what went on behind that door. Apparently Cas had been wrong in his thought for he could hear his own brother on the other side of the door.

"I know it hurts Sam. Trust me I know." What hurts? Cas stepped closer to the door to listen better.

"It's not fair, Gabe. I just-" Sam's sobbing seemed to get a bit harder.

"Yes, Sammy. I know." Castiel heard Gabriel move. He guessed it was to comfort Sam for the next sentence was muffled by what Cas was guessing was his chest.

"I love him but it's not fair." Who did Sam love? Was this how Dean felt when he was confused yesterday? Because Cas didn't like it one bit.

"I know Sammy-" Cas didn't particularly like the way his brother said Sam's name there, "I know just how you feel. And he loves you but not the way you want him to. I get that trust me I do." Gabriel sounded almost as heartbroken as Sam did.

What were they talking about?

Sam's voice was clear once again, "I know you do, Gabe. I'm sorry. It can't be easy for you either."

A sigh. From Gabe. Another from Sam.

"What a pair we make Sammy..."

"Both in love with our brothers yet neither able to have them..."

WHAT? Cas staggered back from the door and looked at it in shock.

"Besides, it's morally wrong anyway. So it doesn't really matter, does it Gabe?"

Castiel was in such a state of shock that instead of vanishing to leave the house he ran. He ran down the stairs, ran across the hallway, and ran out the front door and continued to run until he reached the end of the driveway and stopped; only then remembering that he was an Angel.


	7. Chapter 7

Months had passed and Castiel lived with this new knowledge that his brother loved him and yet said nothing to anyone.

Months passed in which Sam had moved from the house with Dean into his own two bedroom apartment which Cas was sure he shared with Gabriel.

Gabriel who was in love with Castiel while Sam was in love with Dean. And yet the two of them were together.

Is that what Gabriel had meant by they couldn't have what they wanted so they settled for each other?

Cas had felt bad when he figured that out. He and Dean were hurting their brothers with their relationship and yet Dean didn't know it. But Castiel did. And yet he did nothing.

No. That wasn't true...He'd heard- not long after that- another conversation between Gabriel and Sam.

"I have to listen to it every night Gabe...I have to lay there and listen while my brother- the man I love- has sex with Cas damned near every night." Sam had been crying yet again. "And I cry myself to sleep every time!"

It was that conversation that had prompted Gabriel to suggest Sam move out and the younger Winchester had agreed.

And it was also that conversation that had caused Cas to deny Dean sex for the first time that same night.

It had been months since all of this and Dean was currently sitting at the dining room table staring blankly at the coffee cup in his hand while one hand was pressing the phone to his ear.

"Yeah, Sammy it's fine."

"No, I don't mind. It's still your home too."

"No. Why would you think-"

"Right...Sorry...I uh...I guess I never really-"

"Sam that's not fair!"

"Don't!" He sighs now and nods sullenly like the person on the other end can actually see that.

"Yeah, Sammy. See ya in a bit..."

Dean looks almost dejected when he placed his cell phone aside on the table.

"Sam and Gabriel are coming over to get the last of Sam's stuff...I think I'm gonna go lay down for a bit." He starts to rise from the chair when Cas steels his resolve and speaks.

"Dean I think we need to talk." Dean pauses and it almost looks as if he's scared.

"About our brothers."


	8. Chapter 8

As Sam and Gabriel hauled the last of Sam's boxes to the younger Winchester's truck Dean stood at the foot of the stairs watching the pair.

As they worked Dean couldn't keep his eyes off of Sam. Everything Cas had told him it was like Dean was seeing it all. The way Sam avoided looking at him, touching him, only spoke in short clipped sentences. Like doing any of that hurt too much.

And Gabriel...Well nothing seemed to have changed there. Gabriel still messed with Cas but it looked as if it was all forced. Like to be happy in messing with his little brother wasn't what it used to be.

Several times as Sam passed Dean the elder brother wanted to reach out and stop him. Wanted to make Sam look at him. Look him in the eyes and make him talk. He wanted Sam to touch him. Wanted to feel his brother's hand on his arm, on his shoulder, hell in his own hand if he could.

Where that thought came from he'd never know, but it was true none the less.

He never noticed that Sam didn't touch him anymore unless Dean touched him first until after his conversation with Cas.

Once Cas told him everything he'd overheard and what the angel noticed in the several months since Dean sat there and thought over everything that had or hadn't happened since they moved into this house nearly a year ago now.

Sam was handing Gabriel the last box as he came down the stairs and Dean managed to work up enough nerve to snag the sleeve of Sam's shirt, "Sammy, why?"

A surprised gaze landed on Dean's hand and moved to his face. "Why what Dean?"

"Why are you leaving?" The 'again' went unsaid but it wasn't unheard. By either of them.

"I'm just four blocks away Dean. You're more than welcome to come by when you're not busy." Sam shrugged and with that motion Dean's fingers lost purchase on the blue shirt sleeve.

"Sam-"

"Stop Dean, look, you and Cas need your privacy. Besides I'd rather not hear it anymore." Sam took a step back and sighed, "Love you, Dean." And with that- before Dean could reach out and take hold of Sam's wrist- the younger brother left the house, leaving his brother staring after him with a deep frown marring his features.

"Love you too Sammy..."


	9. Chapter 9

**Warning:: Slightly OOC Dean…**

Sleep did come easy that night. And when it did, dreams were odd and confusing.

"This can't be real...This is a dream right?"

"Just because it's a dream doesn't make it any less real Dean." The voice belonged to a petite blonde with green eyes wearing a smurfs night shirt and a pair of boy shorts.

"Jess..."

"Hi Dean."

She was sitting on the edge of the bed she'd shared with Sam at Stanford looking at him with a sympathetic expression that had him feeling like an ass.

"I'd say you should feel that way, but you didn't know."

"What are you-"

"I think you know what I'm talking about Dean."

Yeah, he knew. But why was he having this conversation with his brother's dead girlfriend?

"Because I'm an outside observer and you need perspective."

Okay, how did she keep-

"I'm in your head Dean. This is a dream, I know your thoughts. That's how."

Well then...

"Dean, it was always you."

He sank to the chair in the corner of their room and frowned, "What do you mean?"

"Dean, look at me. Blonde hair, green eyes." His own emerald orbs swept over her and the frown on his lips deepened. "I'm the spitting image of a female you." He looked her in the eyes now, "It was always you."

Dean sighed and leaned forward, elbows resting on his knees and face in his hands.

"Now, do you want the rest of it all? Do you want to hear everything that's been hidden under everything?"

He was a bit lost now.

"You never knew that all you had to do was ask. You forever thought that you couldn't have what you really wanted and then along came innocent Castiel and your affections changed to him. Because he was safe. Because he was better than pining after the brother that you thought was straighter than you were."

Could she blame him? Sam'd been set on marrying Jessica for Christ's sake!

"Be that as it may, you never asked. And when everything was said and done and the two of you settle down and put up the hunting mantle he's ready to tell you. Ready to tell you everything that he loves you in ways a brother shouldn't. He's ready to do just that but he walks into the last motel you two ever stay in and there you are. Having your brains fucked out by your beloved Angel."

That last line sounded wrong coming from Jessica's mouth...

"Poor Loving Sammy. Just had his heart ripped out and you didn't even know you'd done it."

Dean didn't know he'd been crying until Jessica's hand touched his cheek to wipe away tears as they streamed down his face.

Dean found himself moments later on his knees with his face buried in Jessica's shoulder her arms holding him as he cried.

It was several minutes later before Dean could pull himself together long enough to form sentences. "And that's why he's with Gabriel?"

"Yes. They help each other through this. Gabriel knows exactly how Sam feels."

Dean's eyes turned down. "I'd be too late then."

"What makes you think that Dean? Sam still loves you. He told you so himself. He's not in love with Gabriel. Yes he loves the arch angel, but it's not the same."

Jessica made Dean look her in the eyes, "It's never too late. You just need to make sure you're ready for that."


End file.
